CHICAGO -- The first day Jon Lester became a free agent, the Cubs reached out and sent a 15-minute video about the team, its future and why the left-hander was a good fit. And the club didn't stop there.
On Monday, Lester officially joined the Cubs, signing a six-year, $155 million contract, the largest in franchise history. And among the deciding factors were camouflage hats with the Cubs insignia on them and the fact that chairman Tom Ricketts likes to go hunting.
President of baseball operations Theo Epstein and general manager Jed Hoyer knew Lester well. They watched the pitcher grow up in the Red Sox organization, saw him overcome cancer, and recover to win the deciding game in the 2007 World Series. Lester came to Chicago in mid November and Epstein, Hoyer and others delivered their sales pitch.
The Cubs began by showing Lester a model of what Wrigley Field will look like after the renovations are complete. The four-year, $575 million project began in October.

The community relations people talked to Lester about what they could do for the pitcher and his NVRQT foundation. He also was given a presentation about how the team takes care of players' families, from the family room to travel.
"The two things Jon cares most about are family and winning, in that order," Epstein said.
Lester was briefed about the Chicago media, and Epstein joked that was a brief part of the presentation.
The Cubs updated Lester on the travel, how day games will allow him to be home with his family at night.
The final element involved a presentation by the baseball operations department on what Epstein and Hoyer have been doing as far as rebuilding the Cubs.
"The last section was titled, 'Baseball operations: How the Cubs are going to win a World Series with Jon Lester in 2015 and Beyond,'" Epstein said.
Lester saw the Cubs first-hand during an Interleague series at Fenway Park, which Chicago swept. But players like Jorge Soler, Javier Baez and Kyle Hendricks weren't on the active roster at that time.

"We felt good about our process and the genuine connection and his genuine interest in wanting to be here," Epstein said. "If you strip everything else away, we felt like Jon Lester really wants to come here and win a World Series for the next chapter in his career."
At dinner that night at RPM Steak in downtown Chicago, Ricketts met the pitcher and they talked about hunting. Lester said he was impressed by Ricketts' passion for the Cubs.
"He's not your average owner, he's a fan," Lester said. "He grew up a Cubs fan, met his wife in the bleachers. I thought that was really unique and really cool aspect."
Epstein has never gone hunting with Lester, but he was willing to do whatever it took to lure the free agent to Wrigley Field.
"I was ready to soak myself in deer urine if necessary, but I didn't have to," Epstein said.
For the uninitiated, hunters will often use urine to lure deer within range.
"I'll take him hunting, but we're not going to do the deer urine," Lester said when told about Epstein's comments. "It gets on everything around you and it's miserable."
But the Cubs did send Lester some gifts during the courtship, including a camouflage hat with the Cubs insignia on it. Lester said it was a pretty cool gift, and not the usual flowers for the wife or bottle of wine. He even brought that hat on Monday.
"You know they're thinking of you, and it's that little extra message, like, 'Hey, you're on our radar,'" Lester said. "It was cool and stuff we can give our family."
Epstein said they felt good after the day-long session with Lester.
"There was unmistakeable momentum coming out of that meeting," he said.
It wasn't that other teams didn't try. The Giants not only sent manager Bruce Bochy to Lester's Atlanta home, but catcher Buster Posey also stopped by. Red Sox second baseman Dustin Pedroia called Lester often to try and get the lefty to return to Boston.
The Cubs did not go 48 hours without sending another message to either Lester or his agents. During the Winter Meetings in San Diego, Epstein would meet with the Levinsons late at night in their suite.
According to Epstein, another team offered Lester more money but the Cubs annual average value of the deal was most likely the highest.
This was the first time Epstein gave a player a no-trade clause, and he said it would've been difficult to sign Lester without including that.
Such a long-term contract for a pitcher is a risk, and Epstein is well aware of that. But his relationship with Lester helped justify the deal.
"We've been around him since he was 18 so I know exactly what shoulder program he's been on since he was 18, I know how well he's executed that shoulder program, how diligent he's been with it," Epstein said. "I know how his MRIs look like. We signed him to a contract extension [in 2009 with the Red Sox]. His work ethic didn't change one bit, his passion didn't change one bit after signing that contract.
"He's left-handed, and left-handed pitchers in this bucket tend to perform throughout their contracts better than right-handed pitchers," Epstein said. "He's got the right pitch mix to allow him to age gracefully because he doesn't get hitters out one way especially now that his curveball is back in the mix and he's working both sides of the plate and the cutter is one that ages well."
And that's what the Cubs are counting on.
"It doesn't happen every day -- a player taking less let alone to a team that finished in last place," Epstein said. "I think it emphasizes how much he wanted to be here and the fact that he came here for the right reasons, which was important to us."